Chastity Videos - Trans (33,133)

Chastity Fuck with Jennifer Lunden

Chastity Fuck with Jennifer Lunden

FapHouse 2 weeks ago

Oh My God! My Sissy Bride Clit Is Exploding as I Bounce on This Huge Dildo! a Sissybridegasm... Dream

69% 0:39 / 1:55

Oh My God! My Sissy Bride Clit Is Exploding as I Bounce on This Huge Dildo! a Sissybridegasm... Dream

FapHouse 1 month ago

A College Girl at the Pylon. Locked, with a Plug, and Can No Longer Stand Straight

HD 0:39 / 10:46

A College Girl at the Pylon. Locked, with a Plug, and Can No Longer Stand Straight

FapHouse 2 months ago

Maids Interview Reverse Gangbang

Premium HD 40:25

Maids Interview Reverse Gangbang

Sheer 6 days ago

Luna Florez Private Show

55% 4K 2:00 / 16:19

Luna Florez Private Show

Flirt4Free 6 days ago

Trans Homewrecker Is Going to Visit You so You Can Fuck Her While Your Wife Is Away

Trans Homewrecker Is Going to Visit You so You Can Fuck Her While Your Wife Is Away

FapHouse 1 year ago

Sophia Loreen Party on Jun 3, 2026 - Part 3

67% HD 2:00 / 21:53

Sophia Loreen Party on Jun 3, 2026 - Part 3

Flirt4Free 4 months ago

Tiffany Kitten the Sexy Blonde Sissy Crossdresser Babe Shows Her Gorgeous Body and Fucks Her BBC Dildo Part 2

64% HD 1:01 / 6:21

Tiffany Kitten the Sexy Blonde Sissy Crossdresser Babe Shows Her Gorgeous Body and Fucks Her BBC Dildo Part 2

FapHouse 1 year ago

Marian & Richard Private Show

57% HD 2:00 / 1:56:58

Marian & Richard Private Show

Flirt4Free 4 months ago

Good Little Slutty Holes Take Every Inch. (Cum in Chastity Cage)

Good Little Slutty Holes Take Every Inch. (Cum in Chastity Cage)

XNXXGold 1 year ago

Anal Hike

56% HD 1:01 / 17:35

FapHouse 6 months ago

Sophia Loreen Private Show

4K 2:00 / 16:41

Sophia Loreen Private Show

Flirt4Free 1 week ago

Rebeccah Gibson Private Show

Rebeccah Gibson Private Show

Flirt4Free 1 week ago

Ass Fucking in Tiny Chastity

HD 0:39 / 18:43

Ass Fucking in Tiny Chastity

FapHouse 3 years ago

Being bent over and fucked by @XXXGuttersnipe’s Huge BBC 🐰♠️💦💦

68% HD 0:10 / 10:17

Being bent over and fucked by @XXXGuttersnipe’s Huge BBC 🐰♠️💦💦

LoyalFans 4 years ago

Sissy Evolution 2 Be Happy. Be a Bimbo

54% HD 0:39 / 6:09

Sissy Evolution 2 Be Happy. Be a Bimbo

FapHouse 11 months ago

Cute Tgirl in Flat Chastity Clip Fucks Huge Dildo!

56% HD 1:01 / 6:02

Cute Tgirl in Flat Chastity Clip Fucks Huge Dildo!

FapHouse 2 years ago

Male to Female Masked Doll Transformation

74% HD 0:59 / 10:22

Male to Female Masked Doll Transformation

Clips4sale 2 years ago

Sissykanisa Ride on a Monster Dildo Part2

Sissykanisa Ride on a Monster Dildo Part2

FapHouse 1 year ago

Master & Christian & Nicco Private Show

Master & Christian & Nicco Private Show

Flirt4Free 2 years ago

ME CONTRATA UNA CHICA HETERO PARA SU PRIMERA VES CON UNA VERGA TRANS

Premium HD 18:18

ME CONTRATA UNA CHICA HETERO PARA SU PRIMERA VES CON UNA VERGA TRANS

XNXXGold 1 year ago

Sophia Loreen Private Show

4K 2:00 / 29:10

Sophia Loreen Private Show

Flirt4Free 1 week ago

Pretty Busty Bimbo Sissy Kitty and Her Qutoys Dildos Part 1

66% 1:01 / 6:21

Pretty Busty Bimbo Sissy Kitty and Her Qutoys Dildos Part 1

FapHouse 5 months ago

Blonde Trans Fisting Silicone Pussy

HD 0:39 / 12:20

Blonde Trans Fisting Silicone Pussy

FapHouse 1 year ago

Very Hot Goth Femboy Jade Madison Fucked - Compilation 3

61% HD 0:10 / 14:04

Very Hot Goth Femboy Jade Madison Fucked - Compilation 3

LoyalFans 3 months ago

2 Sissy Latex Nurses Getting Pegged in Chastity by MILF Lisa

54% HD 0:39 / 36:16

2 Sissy Latex Nurses Getting Pegged in Chastity by MILF Lisa

FapHouse 2 years ago

Sissy Humiliation Dreams

HD 1:01 / 12:42

Sissy Humiliation Dreams

FapHouse 1 month ago

Sissy Maid Gets Locked in Chastity and *** to Serve2

66% HD 1:01 / 5:55

Sissy Maid Gets Locked in Chastity and *** to Serve2

FapHouse 1 month ago

Sissy Locked and Loaded Extended

HD 1:01 / 34:01

Sissy Locked and Loaded Extended

FapHouse 8 months ago

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

43% HD 0:39 / 4:03

Meet Nikki the Cute Femboy. Tiny Dick Bubble Butt BBC Wild Ride

FapHouse 6 months ago

flamingo orgy 11 t-girls + 1 cis girl + 5 men

HD 1:02 / 51:46

flamingo orgy 11 t-girls + 1 cis girl + 5 men

AnalVids 4 months ago

Troy Khalil Private Show

Troy Khalil Private Show

Flirt4Free 1 year ago

Sloppy Self Foot Worship with Spit Creampie and Cum! - Sissy Jessica Bloom

HD 1:01 / 18:48

Sloppy Self Foot Worship with Spit Creampie and Cum! - Sissy Jessica Bloom

FapHouse 8 months ago

Dom mommy give you a chastity cage Role Play

Premium HD 18:57

Dom mommy give you a chastity cage Role Play

Sheer 1 year ago

Silicone Bodysuit and Pvc Dress. Sucking Dildo & Fucking My Pussy

HD 1:01 / 12:30

Silicone Bodysuit and Pvc Dress. Sucking Dildo & Fucking My Pussy

FapHouse 1 year ago

Dumb Whore Thinks Her Asshole Is Her New Pussy, Maybe Shes Right

Premium HD 5:26

Dumb Whore Thinks Her Asshole Is Her New Pussy, Maybe Shes Right

XNXXGold 5 months ago

Snow White Chantal Sweet - Spritz with Me Baby

64% VR 0:08 / 7:35

Snow White Chantal Sweet - Spritz with Me Baby

FapHouse 4 months ago

Sissy in Flat Chastity Cage and Micro Thong Two Beers via Anal at the Open Door

Sissy in Flat Chastity Cage and Micro Thong Two Beers via Anal at the Open Door

FapHouse 1 year ago

Chastity Slave with Catheter

HD 0:39 / 18:53

Chastity Slave with Catheter

FapHouse 8 months ago

Fem Dom Station

Fem Dom Station

FapHouse 1 year ago

Easter Sissy

Premium HD 15:35

Sheer 2 years ago

Imagine Everything I Can Do for You ;)

HD 2:00 / 29:50

Imagine Everything I Can Do for You ;)

Flirt4Free 7 years ago

SUBMISSIVE SLUT SPANKED, CAGED AND LICKING HIS FEET

Premium HD 18:20

SUBMISSIVE SLUT SPANKED, CAGED AND LICKING HIS FEET

Sheer 4 weeks ago

Chastity Fuckdoll 10 - Gigi

Premium HD 30:25

Chastity Fuckdoll 10 - Gigi

XVideosRed 2 months ago

Plapping Sissy in Chastity Ass Play Fuck Machine JOI CBT Anal Masturbation for Goddess Nikki Kit

49% HD 0:10 / 13:03

Plapping Sissy in Chastity Ass Play Fuck Machine JOI CBT Anal Masturbation for Goddess Nikki Kit

LoyalFans 6 months ago

Chastity Sissy Dildo Riding Anal Orgasms Using Cum as Lube - Jessica Bloom

57% HD 0:39 / 27:42

Chastity Sissy Dildo Riding Anal Orgasms Using Cum as Lube - Jessica Bloom

FapHouse 1 year ago

Rainbow Nyxi Leon Strips to Entice Stud Stepdaddy

61% HD 0:39 / 5:54

Rainbow Nyxi Leon Strips to Entice Stud Stepdaddy

FapHouse 2 years ago

Sabrina Smiith Private Show

49% HD 2:00 / 8:57

Sabrina Smiith Private Show

Flirt4Free 11 months ago

Chain Bikini Warrior Reina Collects Her Magical Cum Essence

HD 1:01 / 28:40

Chain Bikini Warrior Reina Collects Her Magical Cum Essence

FapHouse 6 months ago

From heavy mask to female mask

HD 1:01 / 20:35

From heavy mask to female mask

FapHouse 5 years ago

Sissy Outside and Inside BBC Dildo Play

HD 0:39 / 19:36

Sissy Outside and Inside BBC Dildo Play

FapHouse 6 months ago

Chinese Little Fake Girl Experience 'Caught in the Cage, Machine Dildo'

Chinese Little Fake Girl Experience 'Caught in the Cage, Machine Dildo'

Clips4sale 1 year ago

Dance with my naked and strong body, touch my tight pussy and get it so wet... Let me RIDE your HARD COCK and let me end over it...(squirt)

Dance with my naked and strong body, touch my tight pussy and get it so wet... Let me RIDE your HARD COCK and let me end over it...(squirt)

Flirt4Free 2 years ago

Elvis Rey & Andres & Aron Private Show

HD 2:00 / 14:05

Elvis Rey & Andres & Aron Private Show

Flirt4Free 3 years ago

Busted T-Girls, Natalie Mars, 3on1, BBC, Fisting, DAP, Fisting, Rough, Gapes, Wrecked Ass, Creampie, Cum in Mouth BTG117

Busted T-Girls, Natalie Mars, 3on1, BBC, Fisting, DAP, Fisting, Rough, Gapes, Wrecked Ass, Creampie, Cum in Mouth BTG117

XVideosRed 2 years ago

Colombian Boys Private Show

Colombian Boys Private Show

Flirt4Free 2 years ago

Paulo & Richar & Jose Private Show

66% HD 2:00 / 9:24

Paulo & Richar & Jose Private Show

Flirt4Free 4 months ago

Feeling sexy in hot nylon lingerie, frustrated in chastity ofcourse as we can't have it all can we...

Feeling sexy in hot nylon lingerie, frustrated in chastity ofcourse as we can't have it all can we...

FapHouse 1 year ago

Slave Adashah Locked in a Tiny Chastity. Fucked in the Ass with a Large Vibrator and Masturbated with Small Vibrators

63% HD 0:39 / 5:16

Slave Adashah Locked in a Tiny Chastity. Fucked in the Ass with a Large Vibrator and Masturbated with Small Vibrators

FapHouse 1 year ago

Passiva Gostosa Sendo Dominada por Trans Ativa

Premium HD 11:52

Passiva Gostosa Sendo Dominada por Trans Ativa

XVideosRed 1 year ago

Agora a m&atilde_e dele descobre mesmo ... mais um video com o filho da minha amiga .

Premium HD 22:09

Agora a m&atilde_e dele descobre mesmo ... mais um video com o filho da minha amiga .

XVideosRed 1 month ago

Sophia Loreen Private Show - Part 3

66% 4K 2:00 / 6:09

Sophia Loreen Private Show - Part 3

Flirt4Free 1 year ago

Femboy and Trans Woman Using Fucking Machine - Compilation 1

HD 0:10 / 20:00

Femboy and Trans Woman Using Fucking Machine - Compilation 1

LoyalFans 2 months ago

Goth Tgirl in Transparent Latex Caged Taking Dick

66% HD 0:39 / 19:27

Goth Tgirl in Transparent Latex Caged Taking Dick

FapHouse 2 months ago

Flat Chastity Exhibitionsm Inside Building

63% HD 0:08 / 0:57

Flat Chastity Exhibitionsm Inside Building

FapHouse 1 year ago

Gloryhole Piss Drinker - Sexy Trans Princess Drinks entire glass of piss from mystery cock

Premium HD 2:33

Gloryhole Piss Drinker - Sexy Trans Princess Drinks entire glass of piss from mystery cock

XNXXGold 1 month ago

Hotel Hookup 4 - Esme

Premium HD 23:45

Hotel Hookup 4 - Esme

Sheer 3 months ago

Halloween Party Sex Whore

HD 0:39 / 12:35

Halloween Party Sex Whore

FapHouse 1 week ago

Luna Florez Private Show

Luna Florez Private Show

Flirt4Free 2 weeks ago

Goth Femboy Gapes Ass in Chastity

63% HD 0:39 / 2:26

Goth Femboy Gapes Ass in Chastity

FapHouse 6 months ago

sensual sissy slut stripper puts her fat ass in your face and make a cumshot with her femboy cock - camera tease & explosive crossdresser ejaculation

HD 0:30 / 10:34

sensual sissy slut stripper puts her fat ass in your face and make a cumshot with her femboy cock - camera tease & explosive crossdresser ejaculation

AnalVids 2 weeks ago

nerdy trans girl autumn rain in chastity riding a big dildo

65% HD 0:30 / 10:07

nerdy trans girl autumn rain in chastity riding a big dildo

AnalVids 1 year ago

Kitty vs Bunny

Premium HD 45:10

Sheer 1 year ago

sissy fuckdoll 2

56% HD 0:30 / 18:19

sissy fuckdoll 2

PornBox 2 years ago

Tranny Girly Locked by Stepdaddy! Bad Girl Cheats Until Cumshot!

Tranny Girly Locked by Stepdaddy! Bad Girl Cheats Until Cumshot!

FapHouse 8 months ago

Bimbo Sissy Hucow MILF Visited by Jordan Hung

57% 0:39 / 1:23

Bimbo Sissy Hucow MILF Visited by Jordan Hung

FapHouse 5 months ago

Caged Sissy: Arcade 1st Try

57% HD 0:39 / 7:51

Caged Sissy: Arcade 1st Try

FapHouse 10 months ago

POV W/ Sexy Big Tit Trans Girl Next Door Rachael

POV W/ Sexy Big Tit Trans Girl Next Door Rachael

FapHouse 2 weeks ago

Master & Christian Mckenzie & Christian Rey Private Show

54% HD 2:00 / 11:48

Master & Christian Mckenzie & Christian Rey Private Show

Flirt4Free 3 years ago

Troy Khalil Private Show

59% HD 2:00 / 6:28

Troy Khalil Private Show

Flirt4Free 2 years ago

Sophia Loreen Private Show

Sophia Loreen Private Show

Flirt4Free 3 years ago

Sophia Loreen Party on Aug 21, 2026 - Part 5

68% 4K 2:00 / 2:22:08

Sophia Loreen Party on Aug 21, 2026 - Part 5

Flirt4Free 1 month ago

Nelly Gale Private Show

Nelly Gale Private Show

Flirt4Free 1 week ago

Wrong Room - Femboy Gives BJ POV

HD 0:10 / 11:27

Wrong Room - Femboy Gives BJ POV

LoyalFans 1 week ago

Tiny Cock Locked in Chastity and Dripping Wet Panties

Tiny Cock Locked in Chastity and Dripping Wet Panties

FapHouse 2 years ago

Sexy Cute Sissy Slut, Tiny Clitty Sissygasm in Chastity

Sexy Cute Sissy Slut, Tiny Clitty Sissygasm in Chastity

FapHouse 1 month ago

Caged Trans Slut Gets Dicked Hard

57% 0:39 / 44:40

Caged Trans Slut Gets Dicked Hard

FapHouse 1 month ago

Fat Ass Femboy Fucked in Chastity

Fat Ass Femboy Fucked in Chastity

FapHouse 3 weeks ago

Girl fucks her sissy slut and pissing in small cock cage- Phone version

HD 1:01 / 11:29

Girl fucks her sissy slut and pissing in small cock cage- Phone version

FapHouse 3 years ago

Sophia Loreen Private Show

68% HD 2:00 / 4:29

Sophia Loreen Private Show

Flirt4Free 3 months ago

Spandexfemboy - Anal Addiction with Bbcs - Sissy Chastity Anal Dildo Doggy

Spandexfemboy - Anal Addiction with Bbcs - Sissy Chastity Anal Dildo Doggy

FapHouse 22 hours ago

Rebeccah Gibson Private Show

HD 2:00 / 35:35

Rebeccah Gibson Private Show

Flirt4Free 1 week ago

Milking the Sissy Maid

HD 0:39 / 22:25

Milking the Sissy Maid

FapHouse 9 months ago

Chastity T-Girl Wet, Natalie Mars, DAP, Double Anal Fisting, Wrecked Ass, Almost Rose, Pee Drink, Creampie, Swallow BTG051

Premium 57% 1:02:33

Chastity T-Girl Wet, Natalie Mars, DAP, Double Anal Fisting, Wrecked Ass, Almost Rose, Pee Drink, Creampie, Swallow BTG051

XNXXGold 5 years ago

Lola Crystals and I Having Some Fun

Lola Crystals and I Having Some Fun

FapHouse 3 weeks ago

Sissygasm w Ava Venom

52% HD 0:10 / 8:51

Sissygasm w Ava Venom

LoyalFans 1 year ago

Amber Burnt Private Show

HD 2:00 / 15:06

Amber Burnt Private Show

Flirt4Free 2 years ago

Aron & Master & Elvis Private Show

62% HD 2:00 / 1:53:11

Aron & Master & Elvis Private Show

Flirt4Free 3 years ago

Cum Cum Cum

HD 2:00 / 20:24

Flirt4Free 5 years ago

LOCKTOBER: Submissive Trans Girl, Bella Joie's Locked in Chastity and dominated

63% 0:15 / 26:57

LOCKTOBER: Submissive Trans Girl, Bella Joie's Locked in Chastity and dominated

Clips4sale 3 years ago

Sissy Faggot Cocksucker JOI

56% HD 0:25 / 18:16

Sissy Faggot Cocksucker JOI

Clips4sale 2 years ago

Pegging & Humiliation by DominaFire

HD 1:01 / 13:15

Pegging & Humiliation by DominaFire

FapHouse 3 years ago

I Sandwiches Between Two Machines,they Made Me Creampie so Quickly

HD 0:39 / 13:11

I Sandwiches Between Two Machines,they Made Me Creampie so Quickly

FapHouse 1 year ago

Chastity Fuckdolls Reverse Gangbang 3

Premium HD 35:40

Chastity Fuckdolls Reverse Gangbang 3

XVideosRed 6 months ago

Sissy Maid Gets Locked in Chastity and Strained to Serve1

Sissy Maid Gets Locked in Chastity and Strained to Serve1

FapHouse 1 month ago

Sophia Loreen Private Show

HD 2:00 / 14:29

Sophia Loreen Private Show

Flirt4Free 2 years ago

The Sissy Ghosts Warning

HD 1:01 / 10:55

The Sissy Ghosts Warning

FapHouse 1 week ago

Mandatory Pee

53% HD 0:39 / 2:28

FapHouse 5 months ago

Femdom POV: Sissy

66% 1:01 / 6:27

Femdom POV: Sissy

FapHouse 4 years ago

Sandy Lee Private Show

HD 2:00 / 11:28

Sandy Lee Private Show

Flirt4Free 11 years ago

Goddess Venus Punishes Arrogant Boy Toy

HD 0:39 / 48:08

Goddess Venus Punishes Arrogant Boy Toy

FapHouse 1 year ago

Chastity Locked Sissy Suspended in Red Rope! High Heel Trample, Nipple Play & Prostate Tease!

Premium 4K 1:03:41

Chastity Locked Sissy Suspended in Red Rope! High Heel Trample, Nipple Play & Prostate Tease!

Clips4sale 3 weeks ago

Rubbing a Lips Shaped Chastity Till Orgasm

59% HD 1:01 / 28:09

Rubbing a Lips Shaped Chastity Till Orgasm

FapHouse 7 months ago

Katie Fox TS Compilation Cum 2024 Pt 1

Premium HD 46:44

Katie Fox TS Compilation Cum 2024 Pt 1

XVideosRed 1 year ago

Fisting Little Piggy Lianna Lawson

Premium HD 32:56

Fisting Little Piggy Lianna Lawson

XNXXGold 2 years ago

Pantieboy Taking Long Bc and Fat Bc Dildo. Filling Panties with Cum.

Pantieboy Taking Long Bc and Fat Bc Dildo. Filling Panties with Cum.

FapHouse 22 hours ago

Sophia Loreen Riding and Squirting

Sophia Loreen Riding and Squirting

Flirt4Free 3 years ago

Flat Chastity and Big Dildo

66% HD 0:39 / 18:47

Flat Chastity and Big Dildo

FapHouse 5 months ago

Futa Public Humiliation At Restaurant - Ft Imilia Audley

66% HD 0:30 / 13:15

Futa Public Humiliation At Restaurant - Ft Imilia Audley

Clips4sale 1 year ago

Orgasm in the Chair

HD 1:01 / 17:11

Orgasm in the Chair

FapHouse 4 months ago

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33,133 results found

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