Chastity Videos - Trans (2,861)

THE TRAINING: STRAP-ON, FINGERING & CHASTITY DENIAL

THE TRAINING: STRAP-ON, FINGERING & CHASTITY DENIAL

LoyalFans 2 weeks ago

Very Hot Sissy Fucked - Compilation 2

HD 0:10 / 20:00

Very Hot Sissy Fucked - Compilation 2

LoyalFans 1 month ago

Hot Crossdresser Sucks Big Cock

Hot Crossdresser Sucks Big Cock

LoyalFans 1 month ago

Transbian Voyeur Tease [Femdom Lingerie Chastity]

68% HD 0:10 / 7:46

Transbian Voyeur Tease [Femdom Lingerie Chastity]

LoyalFans 8 months 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 1 year ago

Trans Cowgirl August Harper Rides Adam Castle's Country Cock

HD 0:10 / 27:03

Trans Cowgirl August Harper Rides Adam Castle's Country Cock

LoyalFans 1 year ago

Sissy Cumming in Chastity JOI CEI Cum Eating Instructions

Sissy Cumming in Chastity JOI CEI Cum Eating Instructions

LoyalFans 2 years ago

Sissy Slut School Lesson 2/4: Sissy Training, Double Anal & Double Blowjob Training with Mistress Stellina Obscura

69% HD 0:10 / 14:56

Sissy Slut School Lesson 2/4: Sissy Training, Double Anal & Double Blowjob Training with Mistress Stellina Obscura

LoyalFans 3 months ago

Tranny Foot Slave And Milking Stage 2 (MP4)

Tranny Foot Slave And Milking Stage 2 (MP4)

Clips4sale 1 year ago

TS Natalie Carnot in Chastity, Panel Gagged and Hogtied!

67% 0:35 / 12:55

TS Natalie Carnot in Chastity, Panel Gagged and Hogtied!

Clips4sale 1 year ago

Male to Female Masked Doll Transformation

74% HD 0:59 / 10:22

Male to Female Masked Doll Transformation

Clips4sale 2 years ago

Caned And Fucked Double Domination

Caned And Fucked Double Domination

Clips4sale 3 years ago

Diapers from Your New Trans Cuckysitter

63% 0:24 / 14:41

Diapers from Your New Trans Cuckysitter

Clips4sale 2 years ago

Chastity and Anal Training

72% 0:30 / 20:51

Chastity and Anal Training

Clips4sale 1 year ago

Petite Trans Woman Fucked and Sucking by Bailey Wilde - Compilation 18

HD 0:10 / 20:32

Petite Trans Woman Fucked and Sucking by Bailey Wilde - Compilation 18

LoyalFans 1 month ago

A Sissy Maid Day

54% 4K 0:29 / 20:38

A Sissy Maid Day

Clips4sale 1 year ago

Man Feminized by Roommate as Discipline

HD 0:10 / 10:36

Man Feminized by Roommate as Discipline

LoyalFans 1 month ago

hot trans QoS gets hole destroyed by BBC and spills her cum

65% 0:14 / 17:17

hot trans QoS gets hole destroyed by BBC and spills her cum

Clips4sale 2 years ago

Become My Femme Bestie Fill-In To Date Me

Become My Femme Bestie Fill-In To Date Me

Clips4sale 3 years ago

GIFTING YOU TO MY BLACK KING - LOCKTOBER : LOCKED UP FOR BBC

66% 4K 0:25 / 10:25

GIFTING YOU TO MY BLACK KING - LOCKTOBER : LOCKED UP FOR BBC

Clips4sale 2 years ago

Petite Trans Woman and Crossdresser Bailey Wilde Fucking - Compilation 5

HD 0:10 / 20:02

Petite Trans Woman and Crossdresser Bailey Wilde Fucking - Compilation 5

LoyalFans 1 month ago

Sissy Slut School Lesson 2 of 4: Sissy Training, Double Anal & Double Blowjob Training with Mistress Stellina Obscura

Premium HD 14:56

Sissy Slut School Lesson 2 of 4: Sissy Training, Double Anal & Double Blowjob Training with Mistress Stellina Obscura

Clips4sale 3 months ago

Heavy Rubber Sissy Doll Enjoys Breathplay and Struggles To Cum In Her Cage - Part 2

63% HD 0:10 / 9:15

Heavy Rubber Sissy Doll Enjoys Breathplay and Struggles To Cum In Her Cage - Part 2

LoyalFans 7 months ago

Sissygasm w Ava Venom

52% HD 0:10 / 8:51

Sissygasm w Ava Venom

LoyalFans 1 year ago

Really HOT Trans Woman Fucking Woman *EXCLUSIVE*

65% HD 0:10 / 25:10

Really HOT Trans Woman Fucking Woman *EXCLUSIVE*

LoyalFans 1 month ago

Pool Table Pegging Part 1

61% HD 0:10 / 10:13

Pool Table Pegging Part 1

LoyalFans 8 months ago

reward pegging for latex futa step-mommy's trained chastity sub - SD

reward pegging for latex futa step-mommy's trained chastity sub - SD

Clips4sale 1 year ago

Milking the Futa

Milking the Futa

Clips4sale 1 year ago

Blonde Trans Beauty Fucked by BBC *EXCLUSIVE*

Blonde Trans Beauty Fucked by BBC *EXCLUSIVE*

LoyalFans 1 month ago

SISSY SLUT with pigtails gets FUCKED HARD by BBC and CUMS

Premium HD 13:18

SISSY SLUT with pigtails gets FUCKED HARD by BBC and CUMS

Clips4sale 1 month ago

Live in sissy girls uniform inspection

68% 0:30 / 6:12

Live in sissy girls uniform inspection

Clips4sale 1 year ago

My Sissy Cock Explodes Under Flat Cage

My Sissy Cock Explodes Under Flat Cage

Clips4sale 9 months ago

Petite Trans Woman Fucked and Sucking by Bailey Wilde - Compilation 14

HD 0:10 / 20:06

Petite Trans Woman Fucked and Sucking by Bailey Wilde - Compilation 14

LoyalFans 1 month ago

Goth Tgirl Jade Madison Fucked Doggystyle

57% HD 0:10 / 2:46

Goth Tgirl Jade Madison Fucked Doggystyle

LoyalFans 2 months ago

Natalie Becomes a Living Diaper Doll

54% HD 0:29 / 11:18

Natalie Becomes a Living Diaper Doll

Clips4sale 1 year ago

Sissy Feminized in Lingerie

73% 4K 0:27 / 10:15

Sissy Feminized in Lingerie

Clips4sale 3 years ago

caged sissy rides BBC in pink heels squirts cum out of cage

52% 0:12 / 11:12

caged sissy rides BBC in pink heels squirts cum out of cage

Clips4sale 1 year ago

Convincing You To Become A Controlled Sissy-Girl (SD MP4)

62% 4K 0:31 / 14:50

Convincing You To Become A Controlled Sissy-Girl (SD MP4)

Clips4sale 2 years ago

Worshiping My Latex Mommy's Fat Cock!!!!

Worshiping My Latex Mommy's Fat Cock!!!!

LoyalFans 10 months ago

Post Op Trans Woman Masturbation - Compilation 2

HD 0:10 / 20:02

Post Op Trans Woman Masturbation - Compilation 2

LoyalFans 1 month ago

Panty Soaking Sissygasm - Ballbusting and Vibrator Punishment - HD

65% HD 0:30 / 28:42

Panty Soaking Sissygasm - Ballbusting and Vibrator Punishment - HD

Clips4sale 2 years ago

Hex accepts his fate to become a slutty sissy maid (1080p)

56% HD 0:31 / 18:45

Hex accepts his fate to become a slutty sissy maid (1080p)

Clips4sale 1 year ago

Diapered Sissy Made to Mess & GLUED SHUT

HD 0:10 / 14:42

Diapered Sissy Made to Mess & GLUED SHUT

LoyalFans 4 weeks ago

Locktober Tgirl Fucktoy Double Domination Part 1

Locktober Tgirl Fucktoy Double Domination Part 1

LoyalFans 4 years ago

Sexy Trans Woman Sucking Big Cock POV

Sexy Trans Woman Sucking Big Cock POV

LoyalFans 2 months ago

CROSSDRESSER HUSBAND SURPRISES ME (EN-720)

Premium HD 15:59

CROSSDRESSER HUSBAND SURPRISES ME (EN-720)

Clips4sale 1 week ago

Domme Trainee fucks and creampies his hole

74% HD 0:35 / 17:54

Domme Trainee fucks and creampies his hole

Clips4sale 1 year ago

Subby tgirl railed out by 12inch BBC

54% HD 0:10 / 21:13

Subby tgirl railed out by 12inch BBC

LoyalFans 8 months ago

Strapon Fuck Doll - 720HD

65% 0:15 / 12:16

Strapon Fuck Doll - 720HD

Clips4sale 3 years ago

Tgirl Kala Moon BJ *EXCLUSIVE*

HD 0:10 / 17:19

Tgirl Kala Moon BJ *EXCLUSIVE*

LoyalFans 2 months ago

Blue Bunny Femboy Rope Slave's Punishment Challenge - Ultra-Thin Rope Tight Standing Bind, Hands Wrapped, Mouth Stuffed, Chastity Locked & Cum in Chastity Hogtie Milking Until Exhaustion

Premium 1:04:52

Blue Bunny Femboy Rope Slave's Punishment Challenge - Ultra-Thin Rope Tight Standing Bind, Hands Wrapped, Mouth Stuffed, Chastity Locked & Cum in Chastity Hogtie Milking Until Exhaustion

Clips4sale 8 months ago

Hot Blonde Crossdresser Sucks BBC *EXCLUSIVE*

66% HD 0:10 / 4:02

Hot Blonde Crossdresser Sucks BBC *EXCLUSIVE*

LoyalFans 1 month ago

Step-Bro Caught Crossdressing and Feminized

57% 4K 0:29 / 14:03

Step-Bro Caught Crossdressing and Feminized

Clips4sale 3 years ago

THE 4 STEPS TO A SISSYGASM

THE 4 STEPS TO A SISSYGASM

LoyalFans 2 years ago

Feminization punishment from teacher

53% HD 0:20 / 12:25

Feminization punishment from teacher

Clips4sale 1 year ago

Three Bussy Boys

59% HD 0:10 / 21:03

Three Bussy Boys

LoyalFans 2 years ago

Very Hot Sissy Fucked - Compilation 4

HD 0:10 / 20:01

Very Hot Sissy Fucked - Compilation 4

LoyalFans 1 month ago

Locked Up and Dressed Up for Worship

Locked Up and Dressed Up for Worship

Clips4sale 11 months ago

DIAPERED TGIRL: Tgirl gets diapered changed, chastity and spankings for playing with herself

67% 0:30 / 10:00

DIAPERED TGIRL: Tgirl gets diapered changed, chastity and spankings for playing with herself

Clips4sale 1 year ago

Pussy Free Sissy Pillow Humping JOI

49% HD 0:21 / 10:14

Pussy Free Sissy Pillow Humping JOI

Clips4sale 2 years ago

Fucking Big Ass Sissy in Chastity - Compilation 5

HD 0:10 / 20:13

Fucking Big Ass Sissy in Chastity - Compilation 5

LoyalFans 2 months ago

Caged boytoy gets Milked, Pegged and fed his own cum

66% HD 0:32 / 28:33

Caged boytoy gets Milked, Pegged and fed his own cum

Clips4sale 2 years ago

Throbbing Sissy Cuckold

51% HD 0:10 / 8:38

Throbbing Sissy Cuckold

LoyalFans 1 year ago

plugged, padded, and locked up pup!

plugged, padded, and locked up pup!

Clips4sale 7 months ago

Giada Da Vinci meet LunaFeetCute for one of her first anal experience, anal training, sissy training, chastity

HD 0:33 / 18:01

Giada Da Vinci meet LunaFeetCute for one of her first anal experience, anal training, sissy training, chastity

Clips4sale 2 years ago

FEMINIZED - Encouraged Feminization Play POV - Slut Training with Chastity Lock Up

45% HD 0:33 / 16:20

FEMINIZED - Encouraged Feminization Play POV - Slut Training with Chastity Lock Up

Clips4sale 2 years ago

Fucking Big Ass Sissy in Chastity - Compilation 3

HD 0:10 / 20:04

Fucking Big Ass Sissy in Chastity - Compilation 3

LoyalFans 2 months ago

Flip Fucks R US - TS Becki Bottomz & Jake Grand

HD 0:10 / 41:12

Flip Fucks R US - TS Becki Bottomz & Jake Grand

LoyalFans 2 months ago

Alexxx Hart Pegs Both of Her Submissives Tight Buttholes and Only Releases One from Chastity - ft Brylin Bloom and The XXX Slayer

Alexxx Hart Pegs Both of Her Submissives Tight Buttholes and Only Releases One from Chastity - ft Brylin Bloom and The XXX Slayer

Clips4sale 4 months ago

Tasks From Us Cuckolding

HD 0:25 / 11:23

Tasks From Us Cuckolding

Clips4sale 4 years ago

Extreme Puppy Endurance Hell While Wearing a Flat Chastity Cage and 55mm Gag

Premium 1:04:53

Extreme Puppy Endurance Hell While Wearing a Flat Chastity Cage and 55mm Gag

Clips4sale 9 months ago

oiled trans in flat chastity fucked with BBC and squirts cum

oiled trans in flat chastity fucked with BBC and squirts cum

Clips4sale 2 years ago

SISSY SLUT CHASTITY TRAINING - Compelled Chastity Mind Fuck [Chastity] [Chastity Device] [Chastity Belt] [Male Chastity] [Chastity Cage]

SISSY SLUT CHASTITY TRAINING - Compelled Chastity Mind Fuck [Chastity] [Chastity Device] [Chastity Belt] [Male Chastity] [Chastity Cage]

Clips4sale 1 year ago

Sweet Heavy Rubber Sissy Doll Cums In Chastity

Sweet Heavy Rubber Sissy Doll Cums In Chastity

Clips4sale 1 month ago

Submissive Training III

Submissive Training III

Clips4sale 1 year ago

Foot worship orgasm and cum feeding for TS Girl - [FHD mp4] | Demoness Luna, JuliaTS | Femdom

Foot worship orgasm and cum feeding for TS Girl - [FHD mp4] | Demoness Luna, JuliaTS | Femdom

Clips4sale 7 months ago

Pinky Pinky Feminisation - part 2

65% HD 0:27 / 10:18

Pinky Pinky Feminisation - part 2

Clips4sale 1 year ago

Hospitality Whores ( Full Video 4k )

4K 0:10 / 42:02

Hospitality Whores ( Full Video 4k )

LoyalFans 2 months ago

Step-mom @msjasmine699 catches and punishes trans step-daughter Kassandra 🎀🥵

45% HD 0:10 / 23:49

Step-mom @msjasmine699 catches and punishes trans step-daughter Kassandra 🎀🥵

LoyalFans 6 months ago

7 Day Sissy Tasks Challenge

HD 0:20 / 19:04

7 Day Sissy Tasks Challenge

Clips4sale 2 years ago

Sissies Belong In Chastity (HD MP4)

53% 4K 0:30 / 15:17

Sissies Belong In Chastity (HD MP4)

Clips4sale 2 years ago

Cumeating Prissy Sissies (MP4)

70% 0:29 / 10:30

Cumeating Prissy Sissies (MP4)

Clips4sale 2 years ago

Sissy Ass Inflation

Sissy Ass Inflation

Clips4sale 3 months ago

Submissive Slut Bound and Fucked Part 1

Premium 4K 37:55

Submissive Slut Bound and Fucked Part 1

Clips4sale 1 month ago

Sissy School (1080)

HD 0:21 / 10:04

Sissy School (1080)

Clips4sale 3 years ago

TS Kelly Quell, TS Valorie Valentina & Jake Grand Threeway

HD 0:10 / 23:12

TS Kelly Quell, TS Valorie Valentina & Jake Grand Threeway

LoyalFans 2 months ago

Sleepover with Futanari dolls Reina Hanno & Kanisa

65% HD 0:10 / 19:33

Sleepover with Futanari dolls Reina Hanno & Kanisa

LoyalFans 1 year ago

Medfet shaving genitals after locktober (small4phone)

51% 0:20 / 19:03

Medfet shaving genitals after locktober (small4phone)

Clips4sale 2 years ago

15 days MTF transformation - sissy training - crossdresser - chastity belt - assgasm

42% HD 0:10 / 14:09

15 days MTF transformation - sissy training - crossdresser - chastity belt - assgasm

LoyalFans 1 year ago

Housewife Fucked by Husband's Pool Cleaners

55% HD 0:10 / 26:54

Housewife Fucked by Husband's Pool Cleaners

LoyalFans 10 months ago

POV Mommy Amy changing the sissy Adult Baby diaper and penis cage

POV Mommy Amy changing the sissy Adult Baby diaper and penis cage

Clips4sale 2 years ago

Sissy cuck caught in hotel

53% 0:30 / 34:20

Sissy cuck caught in hotel

Clips4sale 1 year ago

Super Sexy Femboy Bailey Willde Fucked Raw - Compilation 3

HD 0:10 / 20:41

Super Sexy Femboy Bailey Willde Fucked Raw - Compilation 3

LoyalFans 1 month ago

Down Low Guy Fucks Sissy For First Time

HD 0:10 / 22:13

Down Low Guy Fucks Sissy For First Time

LoyalFans 2 months ago

(608) Sissygasm Compilation #01: Crossdresser’s Hands-Free Orgasms - Zoulette (1080p)

(608) Sissygasm Compilation #01: Crossdresser’s Hands-Free Orgasms - Zoulette (1080p)

Clips4sale 1 year ago

Feminization theraphy

Feminization theraphy

Clips4sale 2 years ago

Sissy School Vlog Kitten is Locked Up

61% HD 0:26 / 11:17

Sissy School Vlog Kitten is Locked Up

Clips4sale 2 years ago

My perfect rubberized sissy tutorial

My perfect rubberized sissy tutorial

LoyalFans 4 years ago

Sissy Slave Ruining and Cum Eating

62% HD 0:10 / 25:13

Sissy Slave Ruining and Cum Eating

Clips4sale 4 years 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 2 months ago

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

62% HD 0:27 / 44:35

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

Clips4sale 1 year ago

Sounds and Ballcrushing CBT on Latex Sissy

61% HD 0:10 / 26:25

Sounds and Ballcrushing CBT on Latex Sissy

LoyalFans 3 years ago

Blind Date gone wrong - Sissy seduces a BBC

57% 0:11 / 20:06

Blind Date gone wrong - Sissy seduces a BBC

Clips4sale 2 years ago

Locktober - Plap those pathetic balls

64% 0:30 / 10:52

Locktober - Plap those pathetic balls

Clips4sale 11 months ago

Sissy Window Peg 1 MOV

61% 0:06 / 10:50

Sissy Window Peg 1 MOV

Clips4sale 1 year ago

Tranny Sissy Maid Service Training With Ria Bentley

72% 4K 0:30 / 26:32

Tranny Sissy Maid Service Training With Ria Bentley

Clips4sale 1 year ago

TS Ana Corvida Meets Otto to be Let Out of Self Bondage

66% 0:30 / 16:14

TS Ana Corvida Meets Otto to be Let Out of Self Bondage

Clips4sale 1 year ago

Latex sissy tease - Ass fucked in chastity

Latex sissy tease - Ass fucked in chastity

Clips4sale 2 years ago

Femdom TS Gangbang

HD 0:10 / 24:29

Femdom TS Gangbang

LoyalFans 3 years ago

Alpha couple releases slave couple from chastity and play with their pleasure (1080 EN-sub)

4K 0:38 / 20:40

Alpha couple releases slave couple from chastity and play with their pleasure (1080 EN-sub)

Clips4sale 3 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 9 months ago

going out in public with my lovense remote control vibrator

going out in public with my lovense remote control vibrator

Clips4sale 2 years ago

Lux helps Eliza with Locktober Prep!

HD 0:30 / 10:44

Lux helps Eliza with Locktober Prep!

Clips4sale 1 year ago

Caged Facesitting

Caged Facesitting

Clips4sale 1 year ago

bubble butt slut

bubble butt slut

Clips4sale 2 years ago

Nara have fun with Ts Roberta Cortes and Ts Janny Costa in front of her cuck husband (1080p EN-sub) Cuckold - Hot Wife - Cum Eating - CreamPie - Beta Humiliation - Trans Woman

Premium HD 21:38

Nara have fun with Ts Roberta Cortes and Ts Janny Costa in front of her cuck husband (1080p EN-sub) Cuckold - Hot Wife - Cum Eating - CreamPie - Beta Humiliation - Trans Woman

Clips4sale 2 months ago

Sissy Chastity Tease and Styling wmv

HD 0:11 / 13:22

Sissy Chastity Tease and Styling wmv

Clips4sale 4 years ago

Bisexual encouragement blowing Sissy Doll whore from Prague

Premium 4K 8:02

Bisexual encouragement blowing Sissy Doll whore from Prague

Clips4sale 2 months ago

pov sph BG hot huge cock futa pegs sissy in chastity - SD wmv

pov sph BG hot huge cock futa pegs sissy in chastity - SD wmv

Clips4sale 2 years ago

Post Op Trans Woman Masturbation - Compilation 3

HD 0:10 / 28:11

Post Op Trans Woman Masturbation - Compilation 3

LoyalFans 1 month ago

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