Chastity Videos - Trans (1,659)

Foot Job Freedom

HD 0:10 / 13:00

Foot Job Freedom

LoyalFans 3 weeks ago

Nipple Play, CBT, Chastity and Cross-Dressing

HD 0:10 / 10:32

Nipple Play, CBT, Chastity and Cross-Dressing

LoyalFans 6 months ago

Sensual Sissy Worship mp4

Sensual Sissy Worship mp4

Femdom TS Gangbang

HD 0:10 / 24:29

Femdom TS Gangbang

LoyalFans 2 years ago

She-Male Strokers 18

HD 0:30 / 2:45:00

She-Male Strokers 18

AEBN 19 years ago

Fuckmachine and Throat Training Day

Fuckmachine and Throat Training Day

LoyalFans 2 years ago

trans in chastity gets ass destroyed by BBC fuck machine

Premium 4K 9:14

trans in chastity gets ass destroyed by BBC fuck machine

Clips4sale 3 months ago

Sissy Slut Adventures Volume 1

55% HD 0:10 / 18:39

Sissy Slut Adventures Volume 1

LoyalFans 1 year ago

THROBBING IN THAT COCK CAGE *HD 1080*

HD 0:29 / 13:39

THROBBING IN THAT COCK CAGE *HD 1080*

Clips4sale 2 years ago

Cuck Edging Secrets

Cuck Edging Secrets

LoyalFans 1 year ago

Ep1 Kiara | Test d’une Nouvelle Sissy : De l’Échec Ménager à l’Amour de la Bite & Pegging - Maîtresse Julia

HD 0:10 / 18:24

Ep1 Kiara | Test d’une Nouvelle Sissy : De l’Échec Ménager à l’Amour de la Bite & Pegging - Maîtresse Julia

LoyalFans 2 months ago

Belted up Bitch

65% HD 0:10 / 12:18

Belted up Bitch

LoyalFans 1 year ago

Your just a fucking loser sissy

63% HD 0:30 / 13:02

Your just a fucking loser sissy

Clips4sale 3 years ago

Sounds and Ballcrushing CBT on Latex Sissy

61% HD 0:10 / 26:25

Sounds and Ballcrushing CBT on Latex Sissy

LoyalFans 2 years ago

Shemale putting on chastity cage

Shemale putting on chastity cage

Clips4sale 1 year ago

Sissy Gets Caught

58% 0:30 / 9:26

Sissy Gets Caught

Clips4sale 10 months ago

Devil fucks sissy Barbie in chastity with strapon and firsting - Slut training ATENNA Shelby

Devil fucks sissy Barbie in chastity with strapon and firsting - Slut training ATENNA Shelby

Clips4sale 1 year ago

(4K) Anal Piggy Punishment: Pegging with Chastity, Humiliation, and Deep Fisting (4K)

64% 4K 0:30 / 58:54

(4K) Anal Piggy Punishment: Pegging with Chastity, Humiliation, and Deep Fisting (4K)

Clips4sale 1 year ago

Pious Nuns in Rubber, speak forth the filth within and find sin is so compelling

65% 0:29 / 13:35

Pious Nuns in Rubber, speak forth the filth within and find sin is so compelling

Clips4sale 10 months ago

Sissy Zone Cycle (1080 HD)

57% HD 0:10 / 20:42

Sissy Zone Cycle (1080 HD)

LoyalFans 1 year ago

Sissy Bimbo Dildo Gauntlet - Dolly's First Attempt

HD 0:10 / 13:11

Sissy Bimbo Dildo Gauntlet - Dolly's First Attempt

LoyalFans 1 year ago

Sounds and Ballcrushing CBT on Latex Sissy

59% 0:20 / 26:25

Sounds and Ballcrushing CBT on Latex Sissy

C4S 2 years ago

Latex Bad Dragon Sissy Training

Latex Bad Dragon Sissy Training

LoyalFans 2 years ago

Trans Chastity Beauties Tease With Toys

66% HD 0:30 / 23:37

Trans Chastity Beauties Tease With Toys

Clips4sale 4 months ago

Femdom Interview Trans Kitty Blowjob in Chastity

66% HD 0:10 / 19:02

Femdom Interview Trans Kitty Blowjob in Chastity

LoyalFans 11 months ago

Luci Belle Sissy Threesome

63% HD 0:10 / 25:32

Luci Belle Sissy Threesome

LoyalFans 1 month ago

I fed him viagra while in chastity - then turned him into my slut!

HD 0:10 / 15:42

I fed him viagra while in chastity - then turned him into my slut!

LoyalFans 2 years ago

hot trans in fishnets takes multiple BBC creampies and cums

58% HD 0:14 / 8:07

hot trans in fishnets takes multiple BBC creampies and cums

Clips4sale 11 months ago

Fucking MTF Chastity Charlie

Fucking MTF Chastity Charlie

Clips4sale 2 months ago

BG pegging - fucking and breeding my locked CD sissy bf

BG pegging - fucking and breeding my locked CD sissy bf

LoyalFans 1 year ago

Go Gay For My Girl-Cock (4KUHD MP4)

67% HD 0:32 / 15:55

Go Gay For My Girl-Cock (4KUHD MP4)

Clips4sale 10 months ago

Erica's Punishment Paddling

63% 0:15 / 11:14

Erica's Punishment Paddling

C4S 2 years ago

Pussy Free Loser Pledge 2021

HD 0:10 / 11:43

Pussy Free Loser Pledge 2021

LoyalFans 4 years ago

LITTLE MICRO DICKLIT *HD 1080*

46% HD 0:30 / 12:54

LITTLE MICRO DICKLIT *HD 1080*

Clips4sale 1 year ago

Human Ashtray Extreme Domination

HD 0:29 / 13:25

Human Ashtray Extreme Domination

Fuck Machine Threesome

67% HD 0:50 / 24:06

Fuck Machine Threesome

Clips4sale 9 months ago

720P JOI For The Feminized Sissies Clit: POV, Chastity, Crossdressing, Edging, CEI And Cum Count Down

HD 0:59 / 14:35

720P JOI For The Feminized Sissies Clit: POV, Chastity, Crossdressing, Edging, CEI And Cum Count Down

Clips4sale 1 year ago

Sissy JOI Gooning in Chastity

HD 0:10 / 12:11

Sissy JOI Gooning in Chastity

LoyalFans 2 years ago

My Confused Sissy Boy

65% 1:01 / 23:08

My Confused Sissy Boy

Clips4sale 1 year ago

Gagged Sissy Loves Drooling

70% HD 0:10 / 13:16

Gagged Sissy Loves Drooling

Clips4sale 4 years ago

MILF1867 - Pegging the Bully: Rachel Steele & London River’s Femdom Justice

HD 0:30 / 34:59

MILF1867 - Pegging the Bully: Rachel Steele & London River’s Femdom Justice

Clips4sale 11 months ago

Routine Inspection Full Cut

66% HD 0:10 / 38:09

Routine Inspection Full Cut

LoyalFans 8 months ago

Lady Liberty

50% 0:05 / 9:01

Clips4sale 5 months ago

Sling Fuck Training 1

Sling Fuck Training 1

C4S 2 years ago

trans egirl in pink lingerie BLACKED and busts her balls

trans egirl in pink lingerie BLACKED and busts her balls

Clips4sale 1 year ago

Sub Torment 8

65% 0:06 / 10:06

Four Said Feminization (SD MP4)

57% 4K 0:30 / 15:34

Four Said Feminization (SD MP4)

Clips4sale 1 year ago

Futa Public Humiliation At Restaurant - Ft Imilia Audley

HD 0:30 / 13:15

Futa Public Humiliation At Restaurant - Ft Imilia Audley

Clips4sale 3 months ago

Heavy Rubber Sissy Doll Enjoys Breathplay and Struggles To Cum

65% HD 0:30 / 12:47

Heavy Rubber Sissy Doll Enjoys Breathplay and Struggles To Cum

Clips4sale 7 months ago

Sissy Anal JOI + CEI

47% HD 0:28 / 12:44

Sissy Anal JOI + CEI

Clips4sale 2 years ago

oiled trans in flat chastity fucked with BBC and squirts cum

oiled trans in flat chastity fucked with BBC and squirts cum

Clips4sale 1 year ago

Dani Doll in Chastity in Her Sexy Lingerie and Corset

Dani Doll in Chastity in Her Sexy Lingerie and Corset

Clips4sale 3 months ago

Sissy Bride Wedding Day Part 1 Dressed and Locked

61% 0:11 / 6:14

Sissy Bride Wedding Day Part 1 Dressed and Locked

Clips4sale 2 years ago

Nylon Teased Chastity Slut (MP4)

57% 0:30 / 17:27

Nylon Teased Chastity Slut (MP4)

Clips4sale 1 year ago

Tranny Dom fucks tied and chasted Guy

72% HD 0:30 / 10:41

Tranny Dom fucks tied and chasted Guy

Clips4sale 2 years ago

Fucked by Trans Dominatrix Nadia Isabella

65% 0:11 / 29:21

Fucked by Trans Dominatrix Nadia Isabella

C4S 2 years ago

Don't You Love Hucow Pink and Blue Gals

71% 0:29 / 8:53

Don't You Love Hucow Pink and Blue Gals

Clips4sale 1 year ago

Alpha couple releases slave couple from chastity and play with their pleasure (720 EN-sub)

4K 0:38 / 20:40

Alpha couple releases slave couple from chastity and play with their pleasure (720 EN-sub)

Clips4sale 2 years ago

Big Dungeon Party with Slavena Tiger, Adara Jordyn and Mistress Susi wmv

55% HD 0:11 / 34:44

Big Dungeon Party with Slavena Tiger, Adara Jordyn and Mistress Susi wmv

Clips4sale 3 years ago

Step-Sis Locked Me Up: ThePrincessLuxy Cages Gooner Virgin Step-brother & Prepares him for College Sexual Rejection with Cuckold and Tease & Denial

HD 0:26 / 10:05

Step-Sis Locked Me Up: ThePrincessLuxy Cages Gooner Virgin Step-brother & Prepares him for College Sexual Rejection with Cuckold and Tease & Denial

Clips4sale 2 months ago

Big Dungeon Party with Slavena Tiger, Adara Jordyn, Mistress Susi PART 2 wmv

Big Dungeon Party with Slavena Tiger, Adara Jordyn, Mistress Susi PART 2 wmv

Clips4sale 3 years ago

Trans Doll Pumps Tits and Fucks Ass

67% HD 0:10 / 16:15

Trans Doll Pumps Tits and Fucks Ass

Clips4sale 3 years ago

Sissy Female Supremacist

HD 0:29 / 10:02

Sissy Female Supremacist

Clips4sale 2 years ago

If you feel like a woman, I will help you feminize and yes, my lover will fuck you in your hole too 16 min

55% 0:30 / 16:55

If you feel like a woman, I will help you feminize and yes, my lover will fuck you in your hole too 16 min

Clips4sale 10 months ago

Mrs Nara Sissification Training - Chapter One: Dress like a Bitch (720 EN-sub)

55% HD 0:30 / 18:08

Mrs Nara Sissification Training - Chapter One: Dress like a Bitch (720 EN-sub)

Clips4sale 2 years ago

Sissy Pegging

61% 0:14 / 6:27

Clips4sale 7 months ago

HUSBAND CROSSDRESSER with BBC

HUSBAND CROSSDRESSER with BBC

Clips4sale 1 day ago

Hunted and Caged Part 12 - Prisoner to sissy Transformation 6 with Anna List

4K 0:46 / 10:19

Hunted and Caged Part 12 - Prisoner to sissy Transformation 6 with Anna List

Clips4sale 2 years ago

YOUR LITTLE JERKING PREDICAMENT *HD 1080*

HD 0:35 / 10:09

YOUR LITTLE JERKING PREDICAMENT *HD 1080*

Clips4sale 2 years ago

You are my Next Ugly Big Black Cock Slut

4K 0:29 / 12:55

You are my Next Ugly Big Black Cock Slut

Clips4sale 1 year ago

Strap-On Anal Chastity Slut (MP4 HD)

66% HD 0:30 / 10:46

Strap-On Anal Chastity Slut (MP4 HD)

Clips4sale 7 months ago

Hot Sissygasm Cumpilation - 13 Cumshots in a Row! - SD WMV

Hot Sissygasm Cumpilation - 13 Cumshots in a Row! - SD WMV

Clips4sale 1 year ago

Sissies Belong In Chastity (SD MP4)

60% 4K 0:30 / 15:17

Sissies Belong In Chastity (SD MP4)

Clips4sale 2 years ago

Chastity Prisoner Anal Hooked and Vibed

59% 0:23 / 48:28

Chastity Prisoner Anal Hooked and Vibed

Clips4sale 10 months ago

Sissy Chastity JOI - Unlock and Ruin your Orgasm with Me - wmv

65% 0:31 / 18:04

Sissy Chastity JOI - Unlock and Ruin your Orgasm with Me - wmv

Clips4sale 1 year ago

She Got What She Cummed For - Alyssa Bale And Sinn Sage Trans Lesbian Domination With Chastity Cage and Strapon 1080

HD 0:27 / 44:35

She Got What She Cummed For - Alyssa Bale And Sinn Sage Trans Lesbian Domination With Chastity Cage and Strapon 1080

Clips4sale 3 months ago

TAKE LIKE A GOOD GIRL SLUT WHORE CROSSDRESSER IN COCK CHASTITY

TAKE LIKE A GOOD GIRL SLUT WHORE CROSSDRESSER IN COCK CHASTITY

Clips4sale 2 years ago

HARD GAPE

Clips4sale 1 year ago

Tranny Femdom SPH! Cockless chastity slave is transformed into a two-hole slut!

HD 0:30 / 10:35

Tranny Femdom SPH! Cockless chastity slave is transformed into a two-hole slut!

Clips4sale 6 months ago

Cum in Chastity and Eat It - DICK SHRINKING

65% 0:11 / 9:57

Cum in Chastity and Eat It - DICK SHRINKING

Clips4sale 2 years ago

Pinky Tries To Earn His Release Thru CBT (720p)

68% HD 0:30 / 12:48

Pinky Tries To Earn His Release Thru CBT (720p)

Clips4sale 6 months ago

LITTLE MICRO DICKLIT *HD 1080*

Premium HD 6:44

LITTLE MICRO DICKLIT *HD 1080*

Clips4sale 1 year ago

Make me bi to BBC and teach me how to fuck in chastity my Queen Maisa Pravo

77% 0:41 / 22:55

Make me bi to BBC and teach me how to fuck in chastity my Queen Maisa Pravo

Clips4sale 7 months ago

FemDom Feminization- Dick Sucking Lips Enhancement

68% 0:31 / 5:09

FemDom Feminization- Dick Sucking Lips Enhancement

Clips4sale 1 year ago

Double Domme with TS Nancy

Double Domme with TS Nancy

LoyalFans 3 years ago

LATEX CLAD DOMINA AVA SAVAGE GAPES HER TRANS SLUT

52% 0:11 / 7:15

LATEX CLAD DOMINA AVA SAVAGE GAPES HER TRANS SLUT

Clips4sale 1 year ago

BNWO Sissy Bride Gooning

43% HD 0:29 / 12:01

BNWO Sissy Bride Gooning

Clips4sale 4 months ago

Chastity Cage Spit Roasting (MP4 HD)

HD 0:30 / 10:18

Chastity Cage Spit Roasting (MP4 HD)

Clips4sale 4 months ago

Sissy JOI Gooning in Chastity

HD 0:30 / 12:10

Sissy JOI Gooning in Chastity

Clips4sale 2 years ago

BDSM Session Vol 1

62% 0:30 / 32:00

BDSM Session Vol 1

C4S 5 months ago

Double Domme with TS Nancy

HD 0:10 / 10:00

Double Domme with TS Nancy

LoyalFans 9 months ago

dumb trans slut gets her back blown out by BBC and squirts

61% 0:23 / 21:58

dumb trans slut gets her back blown out by BBC and squirts

Clips4sale 1 year ago

Bound to Cum in Chastity

HD 0:29 / 18:43

Bound to Cum in Chastity

Clips4sale 3 years ago

sissy slut in pink heels fucks her ass and cums in cage

66% 0:12 / 8:33

sissy slut in pink heels fucks her ass and cums in cage

Clips4sale 1 year ago

Go Gay For My Girl-Cock (HD MP4)

63% 4K 0:32 / 15:55

Go Gay For My Girl-Cock (HD MP4)

Clips4sale 10 months ago

FUCKING RUBBERDOLL

64% HD 0:29 / 7:18

FUCKING RUBBERDOLL

Clips4sale 1 year ago

adopted into the sissy lifestyle

adopted into the sissy lifestyle

Clips4sale 2 months ago

TS VIPER HIGH CLASS SUGAR BABY

HD 0:11 / 15:04

TS VIPER HIGH CLASS SUGAR BABY

Clips4sale 3 years ago

Chastity Release Challenge by Tranny Girl! You have to cum in one minute!! GERMAN

57% HD 0:30 / 6:34

Chastity Release Challenge by Tranny Girl! You have to cum in one minute!! GERMAN

Clips4sale 2 years ago

“Pink is the New Black” Feminization Pegging Sissification

“Pink is the New Black” Feminization Pegging Sissification

Clips4sale 1 year ago

DRINK *HD 720*

65% HD 0:30 / 21:39

Clips4sale 2 years ago

Sissy Transformation

Sissy Transformation

Clips4sale 1 year ago

secret sissy weekend with your homewrecker goth gf: Friday

61% HD 0:30 / 11:33

secret sissy weekend with your homewrecker goth gf: Friday

Clips4sale 2 years ago

Education of Sissy Jaquelina by Mistress Antonella

57% HD 0:11 / 31:09

Education of Sissy Jaquelina by Mistress Antonella

Clips4sale 3 years ago

Latex Hitachi Bondage

Premium HD 31:25

Latex Hitachi Bondage

Clips4sale 2 years ago

Step-Bro Caught Crossdressing and Feminized

57% 4K 0:29 / 14:03

Step-Bro Caught Crossdressing and Feminized

Clips4sale 3 years ago

Kigurumi chastity lock transvestite intercourse

Kigurumi chastity lock transvestite intercourse

Clips4sale 3 months ago

Chastity Slut Loves Ball Busting

HD 0:11 / 17:38

Chastity Slut Loves Ball Busting

Clips4sale 4 years ago

► TAME LA BRAT - Ep.1 - Remplir sa bouche - Dame Courbe & Estrojeanne - lezdom, fellation, strapon, chasteté

HD 0:10 / 19:24

► TAME LA BRAT - Ep.1 - Remplir sa bouche - Dame Courbe & Estrojeanne - lezdom, fellation, strapon, chasteté

LoyalFans 10 months ago

Your Last Wank – Locktober Chastity Submission - Jaq Quicksilver - Submit to Alpha Dom Jaq as he permits you one final orgasm before being locked up - sissification, joi, sissy training - 720p mp4

Your Last Wank – Locktober Chastity Submission - Jaq Quicksilver - Submit to Alpha Dom Jaq as he permits you one final orgasm before being locked up - sissification, joi, sissy training - 720p mp4

Clips4sale 1 year ago

Sissy Bella Chastity Compilation 1

63% HD 0:15 / 9:49

Sissy Bella Chastity Compilation 1

Clips4sale 3 years ago

Fucked my submissives sissy's husband ass with my huge strap-on

62% HD 0:21 / 16:36

Fucked my submissives sissy's husband ass with my huge strap-on

Sissy Fucks MASSIVE Dildo for Mistress

Sissy Fucks MASSIVE Dildo for Mistress

C4S 2 years ago

Gagged & Marked Up

42% 0:30 / 12:20

Gagged & Marked Up

C4S 10 months ago

extended chastity device focused episode

HD 0:10 / 31:55

extended chastity device focused episode

LoyalFans 1 year ago

Feminised, Spanked and Jerked off by my Step Aunt!!! - mobile friendly version

Feminised, Spanked and Jerked off by my Step Aunt!!! - mobile friendly version

Clips4sale 2 months ago

Severe Punishment for Dirty Sissy Slut by Harsh Mistress Part 1

65% 0:11 / 13:20

Severe Punishment for Dirty Sissy Slut by Harsh Mistress Part 1

C4S 2 years ago

5 must-have sex toys for sissies - Femdom sissy feminization

HD 0:27 / 15:34

5 must-have sex toys for sissies - Femdom sissy feminization

Clips4sale 4 weeks ago

after the gloryhole: futa femdom sissy chastity & diaper fetish blowjob - SD

after the gloryhole: futa femdom sissy chastity & diaper fetish blowjob - SD

Clips4sale 2 years ago

Two Toy Torment

Two Toy Torment

LoyalFans 1 year ago

2 3 4 5 6

1,659 results found

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